CA2361437A1 - Compositions pharmaceutiques contenant de la nicotine ou un ligand des recepteurs nicotiniques et un inhibiteur de la monamine oxydase et leur application dans le sevrage tabagique - Google Patents
Compositions pharmaceutiques contenant de la nicotine ou un ligand des recepteurs nicotiniques et un inhibiteur de la monamine oxydase et leur application dans le sevrage tabagique Download PDFInfo
- Publication number
- CA2361437A1 CA2361437A1 CA002361437A CA2361437A CA2361437A1 CA 2361437 A1 CA2361437 A1 CA 2361437A1 CA 002361437 A CA002361437 A CA 002361437A CA 2361437 A CA2361437 A CA 2361437A CA 2361437 A1 CA2361437 A1 CA 2361437A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- nicotine
- pyridyl
- azabicyclo
- pharmaceutical composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229960002715 nicotine Drugs 0.000 title claims abstract description 72
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title claims abstract description 72
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 25
- 239000003446 ligand Substances 0.000 title claims abstract description 23
- 239000003112 inhibitor Substances 0.000 title abstract description 4
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 title abstract 2
- 206010059612 Tobacco withdrawal symptoms Diseases 0.000 title abstract 2
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims description 30
- 239000002899 monoamine oxidase inhibitor Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 23
- 241000208125 Nicotiana Species 0.000 claims description 20
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 20
- IALVDLPLCLFBCF-CHWSQXEVSA-N befloxatone Chemical compound O=C1O[C@@H](COC)CN1C1=CC=C(OCC[C@@H](O)C(F)(F)F)C=C1 IALVDLPLCLFBCF-CHWSQXEVSA-N 0.000 claims description 17
- 229950000017 befloxatone Drugs 0.000 claims description 17
- -1 rasageline Chemical compound 0.000 claims description 16
- 230000002441 reversible effect Effects 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 235000015218 chewing gum Nutrition 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229960004644 moclobemide Drugs 0.000 claims description 8
- YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229940112822 chewing gum Drugs 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- SQMNCLANJWZZOG-NSHDSACASA-N (5s)-5-(methoxymethyl)-3-[6-(4,4,4-trifluorobutoxy)-1,2-benzoxazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NOC2=CC(OCCCC(F)(F)F)=CC=C12 SQMNCLANJWZZOG-NSHDSACASA-N 0.000 claims description 4
- JUOSGGQXEBBCJB-UHFFFAOYSA-N Metanicotine Natural products CNCCC=CC1=CC=CN=C1 JUOSGGQXEBBCJB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 229940097496 nasal spray Drugs 0.000 claims description 4
- 239000007922 nasal spray Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JUOSGGQXEBBCJB-GORDUTHDSA-N rivanicline Chemical compound CNCC\C=C\C1=CC=CN=C1 JUOSGGQXEBBCJB-GORDUTHDSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- MXYUKLILVYORSK-UHFFFAOYSA-N (+/-)-allo-lobeline Natural products C1CCC(CC(=O)C=2C=CC=CC=2)N(C)C1CC(O)C1=CC=CC=C1 MXYUKLILVYORSK-UHFFFAOYSA-N 0.000 claims description 3
- MXYUKLILVYORSK-HBMCJLEFSA-N (-)-lobeline Chemical compound C1([C@@H](O)C[C@H]2N([C@H](CCC2)CC(=O)C=2C=CC=CC=2)C)=CC=CC=C1 MXYUKLILVYORSK-HBMCJLEFSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000013066 combination product Substances 0.000 claims description 3
- 229940127555 combination product Drugs 0.000 claims description 3
- ANJTVLIZGCUXLD-UHFFFAOYSA-N ent-cytisine Natural products C1NCC2CN3C(=O)C=CC=C3C1C2 ANJTVLIZGCUXLD-UHFFFAOYSA-N 0.000 claims description 3
- 229960002339 lobeline Drugs 0.000 claims description 3
- 229930013610 lobeline Natural products 0.000 claims description 3
- 238000013268 sustained release Methods 0.000 claims description 3
- 239000012730 sustained-release form Substances 0.000 claims description 3
- ANJTVLIZGCUXLD-BDAKNGLRSA-N (-)-Cytisine Natural products C1NC[C@@H]2CN3C(=O)C=CC=C3[C@H]1C2 ANJTVLIZGCUXLD-BDAKNGLRSA-N 0.000 claims description 2
- VXLBSYHAEKDUSU-JXMROGBWSA-N (2e)-2-(fluoromethylidene)-4-(4-fluorophenyl)butan-1-amine Chemical compound NC\C(=C\F)CCC1=CC=C(F)C=C1 VXLBSYHAEKDUSU-JXMROGBWSA-N 0.000 claims description 2
- SQUNAWUMZGQQJD-UHFFFAOYSA-N 1-(4-ethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one Chemical compound C1=CC(CC)=CC=C1C(=O)C(C)CN1CCCCC1 SQUNAWUMZGQQJD-UHFFFAOYSA-N 0.000 claims description 2
- CLRANNZHQRADST-UHFFFAOYSA-N 1-(5-methoxypyridin-3-yl)-1,4-diazepane Chemical compound COC1=CN=CC(N2CCNCCC2)=C1 CLRANNZHQRADST-UHFFFAOYSA-N 0.000 claims description 2
- SHALYUZFJLUFSL-UHFFFAOYSA-N 1-(5-methoxypyridin-3-yl)-1,5-diazocane Chemical compound COC1=CN=CC(N2CCCNCCC2)=C1 SHALYUZFJLUFSL-UHFFFAOYSA-N 0.000 claims description 2
- LWFPJCHDKSLKOQ-UHFFFAOYSA-N 1-(5-propoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCOC1=CN=CC(N2CCNCCC2)=C1 LWFPJCHDKSLKOQ-UHFFFAOYSA-N 0.000 claims description 2
- JRNYLCIPPWHNEJ-UHFFFAOYSA-N 1-(6-bromopyridin-3-yl)-1,4-diazepane Chemical compound C1=NC(Br)=CC=C1N1CCNCCC1 JRNYLCIPPWHNEJ-UHFFFAOYSA-N 0.000 claims description 2
- GAGCCMIPRTXYNT-UHFFFAOYSA-N 1-(6-chloro-5-methoxypyridin-3-yl)-1,4-diazepane Chemical compound N1=C(Cl)C(OC)=CC(N2CCNCCC2)=C1 GAGCCMIPRTXYNT-UHFFFAOYSA-N 0.000 claims description 2
- GJNNXIYZWIZFRH-UHFFFAOYSA-N 2-(pentylamino)acetamide Chemical compound CCCCCNCC(N)=O GJNNXIYZWIZFRH-UHFFFAOYSA-N 0.000 claims description 2
- PBSFXIHNVFMPNN-UHFFFAOYSA-N 2-pyrrolidin-2-yl-2,3-dihydrofuro[3,2-b]pyridine Chemical compound C1CCNC1C1OC2=CC=CN=C2C1 PBSFXIHNVFMPNN-UHFFFAOYSA-N 0.000 claims description 2
- ITPXKRKCDRCWLZ-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)quinoline Chemical compound C1CCNCCN1C1=CN=C(C=CC=C2)C2=C1 ITPXKRKCDRCWLZ-UHFFFAOYSA-N 0.000 claims description 2
- QYFWZGSVWFHUKX-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-[4-(4,4,4-trifluorobutoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(CCOC)N=C1C1=CC=C(OCCCC(F)(F)F)C=C1 QYFWZGSVWFHUKX-UHFFFAOYSA-N 0.000 claims description 2
- SLNLEPCJCLXEDT-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)-5-azabicyclo[2.2.2]oct-2-ene Chemical compound BrC1=CN=CC(C=2C3CCC(CN3)C=2)=C1 SLNLEPCJCLXEDT-UHFFFAOYSA-N 0.000 claims description 2
- USXYDBGSWSSTGE-UHFFFAOYSA-N 3-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1CC(N2)CCC2C1 USXYDBGSWSSTGE-UHFFFAOYSA-N 0.000 claims description 2
- DWDCLEHDNICBMI-UHFFFAOYSA-N 3-bromocytisine Chemical compound C1C2CNCC1CN1C2=CC=C(Br)C1=O DWDCLEHDNICBMI-UHFFFAOYSA-N 0.000 claims description 2
- NUPUDYKEEJNZRG-LBPRGKRZSA-N 3-ethynyl-5-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound CN1CCC[C@H]1C1=CN=CC(C#C)=C1 NUPUDYKEEJNZRG-LBPRGKRZSA-N 0.000 claims description 2
- WNLCEACHDKGCIF-UHFFFAOYSA-N 3-fluoro-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one Chemical compound C1NCC2C3=C(F)C=CC(=O)N3CC1C2 WNLCEACHDKGCIF-UHFFFAOYSA-N 0.000 claims description 2
- YKTSVZRWKHWINV-UHFFFAOYSA-N 4-[(7-hydroxy-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl)amino]benzonitrile Chemical compound OC1CCC2=C1N=CN=C2NC1=CC=C(C#N)C=C1 YKTSVZRWKHWINV-UHFFFAOYSA-N 0.000 claims description 2
- BZTKEUQYHVFBHM-UHFFFAOYSA-N 4-chloro-n-(3-morpholin-4-ylpropyl)benzamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(=O)NCCCN1CCOCC1 BZTKEUQYHVFBHM-UHFFFAOYSA-N 0.000 claims description 2
- QWXLXVLWDOYVAW-UHFFFAOYSA-N 5-(5-ethynylpyridin-3-yl)-3-azabicyclo[2.2.2]octane Chemical compound C#CC1=CN=CC(C2C3CCC(CN3)C2)=C1 QWXLXVLWDOYVAW-UHFFFAOYSA-N 0.000 claims description 2
- MXUNKHLAEDCYJL-UHFFFAOYSA-N 5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one Chemical compound CC1=CC=CC(N2C(OC(CO)C2)=O)=C1 MXUNKHLAEDCYJL-UHFFFAOYSA-N 0.000 claims description 2
- LQZNYEWCPDVKMC-UHFFFAOYSA-N 5-benzyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one Chemical compound C=1C=C2C(C3)CNCC3CN2C(=O)C=1CC1=CC=CC=C1 LQZNYEWCPDVKMC-UHFFFAOYSA-N 0.000 claims description 2
- WOJZFUYQYWDMCH-UHFFFAOYSA-N 5-methylspiro[1,3-benzodioxole-2,3'-1-azabicyclo[2.2.2]octane] Chemical compound C1N(CC2)CCC2C21OC1=CC=C(C)C=C1O2 WOJZFUYQYWDMCH-UHFFFAOYSA-N 0.000 claims description 2
- ZALOZGRZQMHKEQ-UHFFFAOYSA-N 5-tert-butylspiro[1,3-benzodioxole-2,3'-1-azabicyclo[2.2.2]octane] Chemical compound C1N(CC2)CCC2C21OC1=CC=C(C(C)(C)C)C=C1O2 ZALOZGRZQMHKEQ-UHFFFAOYSA-N 0.000 claims description 2
- PSBVHIOWORWMJO-UHFFFAOYSA-N C1NCC2CC1C1=C2C=C(C#C)C(C#N)=C1 Chemical compound C1NCC2CC1C1=C2C=C(C#C)C(C#N)=C1 PSBVHIOWORWMJO-UHFFFAOYSA-N 0.000 claims description 2
- RBOSSLMMOVBNCD-UHFFFAOYSA-N C1NCC2CC1C1=C2C=C(C(F)(F)F)C(C#N)=C1 Chemical compound C1NCC2CC1C1=C2C=C(C(F)(F)F)C(C#N)=C1 RBOSSLMMOVBNCD-UHFFFAOYSA-N 0.000 claims description 2
- CWRAGTJSJNMKCQ-UHFFFAOYSA-N C1NCC2CC1C1=C2C=C(C(F)(F)F)C(Cl)=C1 Chemical compound C1NCC2CC1C1=C2C=C(C(F)(F)F)C(Cl)=C1 CWRAGTJSJNMKCQ-UHFFFAOYSA-N 0.000 claims description 2
- KVFSHZMDUXXIBY-UHFFFAOYSA-N C1NCC2CC1C1=C2C=C2C(=O)NC(=O)C2=C1 Chemical compound C1NCC2CC1C1=C2C=C2C(=O)NC(=O)C2=C1 KVFSHZMDUXXIBY-UHFFFAOYSA-N 0.000 claims description 2
- MGQATKFFMYTJKY-UHFFFAOYSA-N C=1C=C2C(C3)CNCC3CN2C(=O)C=1C1=CC=CC=C1 Chemical compound C=1C=C2C(C3)CNCC3CN2C(=O)C=1C1=CC=CC=C1 MGQATKFFMYTJKY-UHFFFAOYSA-N 0.000 claims description 2
- 101710191405 Conantokin-G Proteins 0.000 claims description 2
- RPYWXZCFYPVCNQ-RVDMUPIBSA-N DMXB-A Chemical compound COC1=CC(OC)=CC=C1\C=C/1C(C=2C=NC=CC=2)=NCCC\1 RPYWXZCFYPVCNQ-RVDMUPIBSA-N 0.000 claims description 2
- NLPRAJRHRHZCQQ-UHFFFAOYSA-N Epibatidine Natural products C1=NC(Cl)=CC=C1C1C(N2)CCC2C1 NLPRAJRHRHZCQQ-UHFFFAOYSA-N 0.000 claims description 2
- IWVRVEIKCBFZNF-UHFFFAOYSA-N LSM-1636 Chemical compound C1CNC2CCCC3=C2N1C1=CC=C(C)C=C13 IWVRVEIKCBFZNF-UHFFFAOYSA-N 0.000 claims description 2
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 claims description 2
- ILLGYRJAYAAAEW-QMMMGPOBSA-N abt-418 Chemical compound CN1CCC[C@H]1C1=CC(C)=NO1 ILLGYRJAYAAAEW-QMMMGPOBSA-N 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 229950001297 altinicline Drugs 0.000 claims description 2
- HFQMYSHATTXRTC-JTQLQIEISA-N amiflamine Chemical compound C[C@H](N)CC1=CC=C(N(C)C)C=C1C HFQMYSHATTXRTC-JTQLQIEISA-N 0.000 claims description 2
- 229950004939 amiflamine Drugs 0.000 claims description 2
- KRNDIPHOJLIHRI-UHFFFAOYSA-N bazinaprine Chemical compound N#CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 KRNDIPHOJLIHRI-UHFFFAOYSA-N 0.000 claims description 2
- 229950005683 bazinaprine Drugs 0.000 claims description 2
- WZXHSWVDAYOFPE-UHFFFAOYSA-N brofaromine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1CCNCC1 WZXHSWVDAYOFPE-UHFFFAOYSA-N 0.000 claims description 2
- 229950004068 brofaromine Drugs 0.000 claims description 2
- KYCBWEZLKCTALM-UHFFFAOYSA-N caroxazone Chemical compound C1=CC=C2OC(=O)N(CC(=O)N)CC2=C1 KYCBWEZLKCTALM-UHFFFAOYSA-N 0.000 claims description 2
- 229950006044 caroxazone Drugs 0.000 claims description 2
- HTBKFGWATIYCSF-QGXIKSNHSA-N conantokin g Chemical compound NC(=O)C[C@@H](C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C(O)=O)C(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(O)=O)C(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C(O)=O)C(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(O)=O)C(O)=O)NC(=O)[C@H](CC(C(O)=O)C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CN HTBKFGWATIYCSF-QGXIKSNHSA-N 0.000 claims description 2
- KMIROODCYQMZLK-UHFFFAOYSA-N ctk0j1809 Chemical compound C1NCC2CC1C1=C2C=C(F)C(F)=C1 KMIROODCYQMZLK-UHFFFAOYSA-N 0.000 claims description 2
- ANJTVLIZGCUXLD-DTWKUNHWSA-N cytisine Chemical compound C1NC[C@H]2CN3C(=O)C=CC=C3[C@@H]1C2 ANJTVLIZGCUXLD-DTWKUNHWSA-N 0.000 claims description 2
- 229940027564 cytisine Drugs 0.000 claims description 2
- 229930017327 cytisine Natural products 0.000 claims description 2
- 229960002565 eperisone Drugs 0.000 claims description 2
- NLPRAJRHRHZCQQ-IVZWLZJFSA-N epibatidine Chemical compound C1=NC(Cl)=CC=C1[C@@H]1[C@H](N2)CC[C@H]2C1 NLPRAJRHRHZCQQ-IVZWLZJFSA-N 0.000 claims description 2
- CHDGAVDQRSPBTA-UHFFFAOYSA-N esuprone Chemical compound CC1=C(C)C(=O)OC2=CC(OS(=O)(=O)CC)=CC=C21 CHDGAVDQRSPBTA-UHFFFAOYSA-N 0.000 claims description 2
- 229950007673 esuprone Drugs 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 229960003980 galantamine Drugs 0.000 claims description 2
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 2
- SDIFKXLSGXCGEN-WJUBNSBASA-L gantacurium chloride Chemical compound [Cl-].[Cl-].C1([C@H]2C3=CC(OC)=C(OC)C=C3CC[N@+]2(C)CCCOC(=O)/C=C(\Cl)C(=O)OCCC[N@@+]2(CCC=3C=C(C(=CC=3[C@H]2CC=2C=C(OC)C(OC)=C(OC)C=2)OC)OC)C)=CC(OC)=C(OC)C(OC)=C1 SDIFKXLSGXCGEN-WJUBNSBASA-L 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 2
- 229950005862 lazabemide Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 229950000928 milacemide Drugs 0.000 claims description 2
- 229950010854 mofegiline Drugs 0.000 claims description 2
- JZXRLKWWVNUZRB-UHFFFAOYSA-N n-(2-aminoethyl)-5-chloropyridine-2-carboxamide Chemical compound NCCNC(=O)C1=CC=C(Cl)C=N1 JZXRLKWWVNUZRB-UHFFFAOYSA-N 0.000 claims description 2
- 229960001779 pargyline Drugs 0.000 claims description 2
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 229950002220 pirlindole Drugs 0.000 claims description 2
- YRVIKLBSVVNSHF-JTQLQIEISA-N pozanicline Chemical compound CC1=NC=CC=C1OC[C@H]1NCCC1 YRVIKLBSVVNSHF-JTQLQIEISA-N 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- LVQTUXZKLGXYIU-GWSNJHLMSA-M rapacuronium Chemical compound [Br-].N1([C@@H]2[C@@H](OC(C)=O)C[C@@H]3CC[C@H]4[C@@H]5C[C@@H]([C@@H]([C@]5(CC[C@@H]4[C@@]3(C)C2)C)OC(=O)CC)[N+]2(CC=C)CCCCC2)CCCCC1 LVQTUXZKLGXYIU-GWSNJHLMSA-M 0.000 claims description 2
- 229960003335 rapacuronium bromide Drugs 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical group C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims description 2
- FTKTZRKAVSDSRA-UHFFFAOYSA-N sercloremine Chemical compound C1CN(C)CCC1C1=CC2=CC(Cl)=CC=C2O1 FTKTZRKAVSDSRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- XYHQFFUUHZUZLL-UHFFFAOYSA-N spiro[1,3-benzodioxole-2,3'-1-azabicyclo[2.2.2]octane] Chemical compound O1C2=CC=CC=C2OC1(C1)C2CCN1CC2 XYHQFFUUHZUZLL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- MKTAGSRKQIGEBH-SSDOTTSWSA-N tebanicline Chemical compound C1=NC(Cl)=CC=C1OC[C@@H]1NCC1 MKTAGSRKQIGEBH-SSDOTTSWSA-N 0.000 claims description 2
- 229960002309 toloxatone Drugs 0.000 claims description 2
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- SJMARDNVEMZJDZ-UHFFFAOYSA-N 5-(1,3-thiazol-2-yl)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one Chemical compound C=1C=C2C(C3)CNCC3CN2C(=O)C=1C1=NC=CS1 SJMARDNVEMZJDZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/465—Nicotine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Addiction (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Nouvelles compositions pharmaceutiques comprenant de la nicotine ou un ligand des récepteurs nicotiniques ainsi qu'un inhibiteur de la monoamine oxydase, destinées au sevrage tabagique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/01144 | 1999-02-02 | ||
| FR9901144A FR2788982B1 (fr) | 1999-02-02 | 1999-02-02 | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| PCT/FR2000/000193 WO2000045846A1 (fr) | 1999-02-02 | 2000-01-28 | Compositions pharmaceutiques contenant de la nicotine ou un ligand des recepteurs nicotiniques et un inhibiteur de la monamine oxydase et leur application dans le sevrage tabagique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2361437A1 true CA2361437A1 (fr) | 2000-08-10 |
Family
ID=9541474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002361437A Abandoned CA2361437A1 (fr) | 1999-02-02 | 2000-01-28 | Compositions pharmaceutiques contenant de la nicotine ou un ligand des recepteurs nicotiniques et un inhibiteur de la monamine oxydase et leur application dans le sevrage tabagique |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1150715A1 (fr) |
| JP (1) | JP2002536342A (fr) |
| AR (1) | AR028983A1 (fr) |
| AU (1) | AU2298800A (fr) |
| CA (1) | CA2361437A1 (fr) |
| FR (1) | FR2788982B1 (fr) |
| HU (1) | HUP0201279A2 (fr) |
| WO (1) | WO2000045846A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7244745B2 (en) | 2002-08-30 | 2007-07-17 | Memory Pharmaceuticals Corp. | Heterocyclic compounds, methods for the preparation thereof, and uses thereof |
| US7396833B2 (en) | 2003-12-22 | 2008-07-08 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US7429664B2 (en) | 2002-09-25 | 2008-09-30 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| US7488737B2 (en) | 2004-04-22 | 2009-02-10 | Memory Pharmaceutical Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| US7625924B2 (en) | 2004-12-22 | 2009-12-01 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
| US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| US8263619B2 (en) | 2004-03-25 | 2012-09-11 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6605610B1 (en) * | 1997-12-31 | 2003-08-12 | Pfizer Inc | Aryl fused azapolycyclic compounds |
| HRP20050506A2 (en) * | 1997-12-31 | 2006-03-31 | Pfizer Products Inc. | Aryl fused azapolycyclic compounds |
| JP2002531456A (ja) | 1998-11-27 | 2002-09-24 | ニューロサーチ、アクティーゼルスカブ | 8−アザビシクロ〔3.2.1〕オクト−2−エン及び−オクタン誘導体 |
| IL137937A0 (en) * | 1999-08-27 | 2001-10-31 | Pfizer Prod Inc | A pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal |
| NZ524202A (en) * | 2000-10-13 | 2004-08-27 | Neurosearch As | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
| RU2282619C9 (ru) * | 2001-04-20 | 2006-12-20 | Пфайзер Продактс Инк. | Способы получения замещенных арилконденсированных азаполициклических соединений, промежуточные продукты и способы их получения |
| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| PT1441708E (pt) | 2001-11-05 | 2009-06-18 | Krele Pharmaceuticals Llc | Composições e métodos para aumentar a observância de terapias utilizando inibidores da aldeído desidrogenase e para tratar alcoolismo |
| US7417049B2 (en) | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
| JP4511196B2 (ja) * | 2002-04-18 | 2010-07-28 | アストラゼネカ・アクチエボラーグ | チエニル化合物 |
| HK1080470B (zh) * | 2002-04-18 | 2008-03-07 | Astrazeneca Ab | 杂环化合物 |
| ES2708552T3 (es) | 2002-12-20 | 2019-04-10 | Niconovum Ab | Método para la preparación de un material particulado que contiene nicotina con una celulosa cristalina (en particular MCC) |
| IL155666A (en) * | 2003-04-29 | 2013-12-31 | Neurim Pharma 1991 | Insomnia treatment |
| DE10338174A1 (de) | 2003-08-20 | 2005-03-24 | Lts Lohmann Therapie-Systeme Ag | Transdermale Arzneimittelzubereitungen mit Wirkstoffkombinationen zur Behandlung der Parkinson-Krankheit |
| US7459469B2 (en) | 2004-11-10 | 2008-12-02 | Targacept, Inc. | Hydroxybenzoate salts of metanicotine compounds |
| WO2007100430A2 (fr) * | 2006-01-27 | 2007-09-07 | Yale University | Analogues de cystisine et d'acétylcholine et procédés de traitement des troubles de l'humeur |
| JP5694645B2 (ja) | 2006-03-16 | 2015-04-01 | ニコノヴァム エービーNiconovum Ab | 改善された嗅ぎたばこ組成物 |
| TWI389889B (zh) | 2006-05-09 | 2013-03-21 | Targacept Inc | (2s)-(4e)-n-甲基-5-〔3-(5-異丙氧基吡啶)基〕-4-戊烯-2-胺之新穎多晶型 |
| EP2021325A2 (fr) | 2006-05-09 | 2009-02-11 | AstraZeneca AB | Formes de sel de (2s)-(4e)-n-méthyl-5-[3-(5-isopropoxypyridin)yl]-4-penten-2-amine |
| US20100028447A1 (en) * | 2007-01-22 | 2010-02-04 | Targacept, Inc. | Intranasal, Buccal, And Sublingual Administration Of Metanicotine Analogs |
| WO2009058120A1 (fr) * | 2007-11-02 | 2009-05-07 | Sri International | Modulateurs des récepteurs nicotiniques de l'acétylcholine |
| US8697722B2 (en) * | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| CN102905527B (zh) | 2010-01-11 | 2016-08-24 | 阿斯特来亚治疗有限责任公司 | 烟碱型乙酰胆碱受体调节剂 |
| SG185497A1 (en) | 2010-05-20 | 2012-12-28 | Astrazeneca Ab | New process for the preparation of aryl substituted olefinic amines |
| US20130165511A1 (en) | 2010-09-01 | 2013-06-27 | TONIX Pharmaceuticals Holding Corp | Treatment for cocaine addiction |
| US10653639B2 (en) * | 2016-05-16 | 2020-05-19 | Cv Sciences, Inc. | Pharmaceutical formulations containing cannabidiol and nicotine for treating smokeless tobacco addiction |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2446895A (en) * | 1994-04-22 | 1995-11-16 | Assistance Publique - Hopitaux De Paris | Use of mao-a inhibitors for the manufacture of a medicament in the treatment of tobacco withdrawal symptoms in smokers |
| US5803081A (en) * | 1996-06-28 | 1998-09-08 | Regent Court Technologies | Tobacco and related products |
-
1999
- 1999-02-02 FR FR9901144A patent/FR2788982B1/fr not_active Expired - Fee Related
-
2000
- 2000-01-28 JP JP2000596965A patent/JP2002536342A/ja not_active Withdrawn
- 2000-01-28 HU HU0201279A patent/HUP0201279A2/hu unknown
- 2000-01-28 CA CA002361437A patent/CA2361437A1/fr not_active Abandoned
- 2000-01-28 EP EP00901660A patent/EP1150715A1/fr not_active Withdrawn
- 2000-01-28 WO PCT/FR2000/000193 patent/WO2000045846A1/fr not_active Ceased
- 2000-01-28 AU AU22988/00A patent/AU2298800A/en not_active Abandoned
- 2000-01-31 AR ARP000100404A patent/AR028983A1/es not_active Application Discontinuation
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| US7994199B2 (en) | 2002-08-30 | 2011-08-09 | Memory Pharmaceuticals Corporation | Heterocyclic compounds, methods for the preparation thereof, and uses thereof |
| US7244745B2 (en) | 2002-08-30 | 2007-07-17 | Memory Pharmaceuticals Corp. | Heterocyclic compounds, methods for the preparation thereof, and uses thereof |
| US7700630B2 (en) | 2002-08-30 | 2010-04-20 | Memory Pharmaceuticals Corporation | Heterocyclic compounds, methods for the preparation thereof, and uses thereof |
| US7943773B2 (en) | 2002-09-25 | 2011-05-17 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| US8252811B2 (en) | 2002-09-25 | 2012-08-28 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| US7429664B2 (en) | 2002-09-25 | 2008-09-30 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
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| US7790722B2 (en) | 2003-12-22 | 2010-09-07 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US8158629B2 (en) | 2003-12-22 | 2012-04-17 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US7396833B2 (en) | 2003-12-22 | 2008-07-08 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US8263619B2 (en) | 2004-03-25 | 2012-09-11 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| US8486937B2 (en) | 2004-03-25 | 2013-07-16 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and use thereof |
| US8691841B2 (en) | 2004-03-25 | 2014-04-08 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and use thereof |
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| US7488737B2 (en) | 2004-04-22 | 2009-02-10 | Memory Pharmaceutical Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| US7625924B2 (en) | 2004-12-22 | 2009-12-01 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| US8273891B2 (en) | 2006-09-22 | 2012-09-25 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2788982A1 (fr) | 2000-08-04 |
| JP2002536342A (ja) | 2002-10-29 |
| EP1150715A1 (fr) | 2001-11-07 |
| WO2000045846A1 (fr) | 2000-08-10 |
| AU2298800A (en) | 2000-08-25 |
| AR028983A1 (es) | 2003-06-04 |
| FR2788982B1 (fr) | 2002-08-02 |
| HUP0201279A2 (en) | 2002-09-28 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |